ChemicalBook CAS DataBase List (1-METHYL-1H-IMIDAZOL-5-YL)METHANOL

(1-METHYL-1H-IMIDAZOL-5-YL)METHANOL synthesis

12synthesis methods

Product Name:(1-METHYL-1H-IMIDAZOL-5-YL)METHANOL
CAS Number:38993-84-9
Molecular formula:C5H8N2O
Molecular Weight:112.13

39021-62-0

38993-84-9

General procedure for the synthesis of 1-methyl-1H-imidazol-5-yl)methanol from 1-methyl-1H-5-formyl-imidazole: 1-methyl-1H-5-formyl-imidazole (4.0 g, 15 mmol) was suspended in tetrahydrofuran (THF) (10 mL) and the resulting solution was cooled to 0 °C. Lithium aluminum hydride (300 mg, 32.0 mmol) was added in batches over 10 min and the resulting suspension was continued to be stirred for 10 min. Under vigorous stirring, the excess hydride was quenched by bulk addition of solid Na2SO4-10H2O (~1 g). Additional THF was added as needed to prevent the slurry from solidifying. The resulting suspension was continued to be stirred for 1 h. Subsequent filtration to remove the sulfate and solvent removal under reduced pressure afforded the target alcohol (1.3 g, 80% yield).1H NMR (400 MHz, CD3OD): δ 7.57 (s, 1H), 6.89 (s, 1H), 4.58 (s, 2H), 3.72 (s, 3H).13C NMR (100 MHz. CD3OD): δ140.1,132.7,128.1,31.9,31.0.

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38993-84-9
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Yield: 73%

Reaction Conditions:

with lithium aluminium tetrahydride in tetrahydrofuran at 20; for 16 h;

Steps:

8
S-Methyl-SH-imidazole^-carboxylic acid ethyl ester (Chem. Pharm. Bull, 1994, 42,1463) (0.62 g, 4.02 mmol) in THF (5mL) was added dropwise over 1 min. to a slurry of lithium aluminum hydride (0.25 g, 6.60 mmol) in THF (20 mL). After stirring 16h at room temperature, the reaction was carefully quenched with excess sodium sulfate decahydrate, dried with anhydrous sodium sulfate and filtered through Celite. Concentration gave 0.33 g (73%) of (3- methyl-3H-imidazol-4-yl)-methanol as a white solid which had: NMR (CDCI₃) δ 7.38 (s, 1 H), 6.87 (s, 1 H), 4.60 (s, 2H)₁ 3.69 (s, 3H). A solution of this alcohol (0.150 g, 1.34 mmol) in thionyl chloride (5 mL) was refluxed for 3 h and concentrated. The residue was dissolved in a minimum of ethanol and ether was added to precipitate a white solid. This was collected to yield 0.185 g (83%) of 5-chloromethyl-1-methyl-1H-imidazole hydrochloride which had: NMR (DMSOd₆) δ 9.15 (s, 1 H), 7.75 (d, J = 1.2 Hz, 1 H), 4.99 (s, 2H), 3.84 (s, 3H).

References:

PFIZER PRODUCTS INC. WO2007/34277, 2007, A1 Location in patent:Page/Page column 58

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38993-84-9
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$18.00/250mg

References